HCID 178418361, compound → HCID 178490516, compound

HRID 2225573Notes

Reaction equation

HRID 2225573 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:21])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[CH2:4][CH2:3]1.[H][H]>CO.[C].[Pd]>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9](=[O:21])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178490515HCID 178490515, compound

Product 1

HCID 178490516HCID 178490516, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

0.075 g of 10% palladium-carbon was added to a solution of 1.5 g of N-(trans-4-methylcyclohexyl)-4-hydroxy -3-methoxycinnamamide (Example 131) in 100 ml of methanol. The solution was vigorously stirred for 16 hours under normal-pressure hydrogen gas. After reaction, the catalyst was filtered out, and the solvent was removed in vacuo from the flitrate, yielding 1.33 g of N-(trans-4-methylcyclohexyl)-3-(4-hydroxy-3-methoxyphenyl)propionamide (a compound of the present as a colorless oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered out
  3. customthe solvent was removed in vacuo from the flitrate

Sources & evidence

ORD record
ord-4845c65035e246fb97475f70d01d3094
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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